


Casual Friday

by Fudgyokra



Category: Batman - All Media Types
Genre: Aged-Up Character(s), Bottoming from the Top, Crossdressing, Exhibitionism, Lingerie, M/M, Mildly Dubious Consent, Mirror Sex, Plot What Plot/Porn Without Plot, Public Sex
Language: English
Status: Completed
Published: 2019-11-03
Updated: 2019-11-03
Packaged: 2021-01-18 19:04:56
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,224
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21281738
Author URL: https://archiveofourown.org/users/Fudgyokra/pseuds/Fudgyokra
Summary: (310): Heels with jeans turned Casual Friday into Casual Sex With My Boss Friday.
Relationships: Tim Drake/Damian Wayne
Comments: 8
Kudos: 215
Collections: Tim Drake





	Casual Friday

**Author's Note:**

> This extremely self-indulgent fic was supposed to be for Kinktober but wasn't finished in time.
> 
> Did a fun little challenge where I tried not to change much from the original draft. I tend to nitpick and didn't wanna waste time overworking what was supposed to be an attempt to blow off steam after all those prompt fills, lol.
> 
> [Tim's lingerie](https://cdn.pornpics.com/pics/2014-10-10/154895_03big.jpg) (NSFW!)

Tim definitely isn’t teetering in his shoes, because that would be ridiculous. He is a master-class fighter, light on his feet and quick with his reflexes. He should be able to wear a pair of high heels.

“What are you doing?” a voice asks. Tim doesn’t have to look to know it’s Jason, and he thanks his lucky stars he already tugged his jeans on so he hadn’t been caught in the lacy red things beneath. He knows the fishnets are visible on his feet, but he hopes he won’t be asked about his choice of underwear.

“What does it look like I’m doing?” He’s a bit on edge, considering what he has planned, but he has to tamp that down before he sets things in motion or risk commentary from his jackass boss at the office. Not the good kind of commentary, either, like he’s going for, but the kind that makes him grit his teeth to keep insults at bay.

It’s no secret he doesn’t like his boss, specifically because it’s Damian, of all idiots in the world. Bruce gave him charge of Wayne Industries the day after he turned eighteen, effectively shoving Tim back to his roots in tech. Not only was it humiliating, it was aggravating having to deal with the kid’s smug grin following him around, giving him more orders than he did to the other employees specifically because he knew it grated Tim’s nerves.

Today he intends to put a stop to that.

He’s no idiot; he has seen the way Damian looks at him when he thinks Tim isn’t aware. From the corner of his eye, he always notices the stare, traveling up and down his body to size him up for something besides combat. He had gotten plenty of _that _look from their childhood, so this was certainly a change of pace. Not subtle, because Damian doesn’t yet know how to hide his interest in things like that. Tim plans to take full advantage. Sure, it’s mean, but he wasn’t the first one to play dirty.

Jason watches Tim toddle around the bedroom, looking unamused with his arms crossed and one brow lifted above the tilt of his frown. “You’re like a lamb,” he says, “and not in the cute way.”

Tim blushes furiously but doesn’t respond. Instead, he keeps trying to walk a straight line, nearly careening to the floor when he trips on a loose article of clothing and then succumbs to the shame of Jason having to catch him. “I should have practiced before now.” It’s as much of an acquiescence as he is willing to give, but he doesn’t expect the sigh he earns.

Jason shakes his head. “Let me help.” When he stands Tim upright, he returns the younger man’s dubiety with a scoff and: “I know my way around a pair of heels, idiot.”

Going by the defensive way Jason talks and lets his darting eyes give him away, Tim chooses not to ask why. “Okay,” he caves, “I have a couple hours before I need to go in for work.”

“And?” Jason asks, smirking now.

It’s Tim’s turn to sigh, far more deeply and resigned than Jason’s had been. “All right. Show me how, Master of Cross-Dressing.” As expected, Jason’s smirk becomes a sneer. Tim beams when he adds, “If you’re good, I might even say thank you.”

* * *

Fishnets are irritating, but they get the job done, he finds.

Phase one moves forward like clockwork. Whenever Damian comes to besiege him in his cubicle, more often than not with an armful of paperwork, Tim makes sure to slide out from underneath his desk with one long, graceful press of his heel down in the carpet.

The shoes are visible from a mile away, especially given Tim’s usual nondescript office attire, which they all wear on weekdays. Today, instead of his typical wingtips, he had purposefully weaponized himself with glossy, red Louboutins. He thanks his trust fund for allowing him the odd frivolity.

While he checks things over, glancing above the stack he’d been given, he carefully crosses his legs, one thigh over the other, allowing the fabric of his jeans to pull taut. He prefers his slacks, but denim does wonders for his body, or so he’s been told.

Damian stares each time it happens, then acts like he wasn’t when Tim meets his gaze again, his own face passive. “I’ll have it done before lunch,” he mumbles, acting annoyed as he tacks on a facetious, “_boss._”

No response before Damian books it back to his office. Tim allows himself a self-satisfied smile.

Phase two arrives at noon, when he can surreptitiously wheel himself away from his computer and walk down the hallway toward Damian’s office. It’s vacated while the man picks up his lunch from the commons area, and Tim chooses the precise moment he’s on his way back, leading them to a confrontation in the hall the second he plops the finished paperwork in the bin on the door.

“Sorry,” he lies, looking up the several inches Damian has on him, “I’m a bit late getting these to you.”

Damian tries and fails to remain stern. There is obvious color in his cheeks. “Don’t let it happen again.”

When Tim turns like Jason taught him and clacks his way down the hall with model-like professionalism, he can feel the heat of those eyes on him, and decidedly spares a glance back during the split-second it takes him to turn the corner. Sure enough, Damian is looking. Abruptly, like he’d been caught doing something wrong, he shoves the office door open with a scowl and disappears inside.

Curiously, Tim tingles from head to toe for the rest of the work day.

Phase three is what brings on the nerves. He can’t let them show, so he’s careful to sit and breathe in his cubicle until the timer ticks down and he can run the last of the day’s progress by his so-called superior.

He has to slip by the employees pooling toward the exit, nodding sympathetically at the few stragglers who would be working well into the evening.

By the time he makes it to the boss’s door this time, there’s a knot in his throat he forces himself to swallow. No time for hesitation. If the overgrown brat catches the slightest hint of anxiety from him, he’ll never hear the end of it.

He walks in without knocking, and when Damian thunks his hand loudly against the underside of his desk and hisses a curse, Tim’s nervousness is replaced with a burning sense of victory, mingling with a touch of something else he’s surprised to feel trickling into the pit of his stomach. He makes his reactionary shaky breath remain in his throat and leaves the door open while he sits on the sofa in front of the desk.

“About this evening’s meeting,” he begins, moving his attention from the soft thump of the door against the wall as it fell fully open to the slight but damning shine on Damian’s palm. The feeling in his stomach grows, because he _knows _what Damian had been doing before he busted in, and the heady notion of almost catching him in the act does things to him he can’t explain. Even the flush on his boss’s face is more obvious than before. He can’t possibly think he’s hiding it from Tim, not this time.

Looking about as guilty as any man can, Damian answers, with a roughness to his voice Tim enjoys, “What about it is so important you couldn’t have bothered to knock?”

“The timing isn’t great,” he answers easily, like he has practiced a hundred times in the mirror back at the Manor. It’s a lie, but it’ll get him where he needs to go.

“What do you mean?” Damian can’t move to wipe his hand without looking suspicious, and so sets it back in his lap with a grimace he fails to hide. “There aren’t any other matters to—”

“I put it in your schedule myself,” Tim says with a haughty tone he knows raises Damian’s blood pressure. “It would be your own fault if you didn’t heed it.”

Predictably, Damian snaps, “I have checked. There is nothing else in my timetable. It must have been an indiscretion on _your _behalf if…” He trails off. An oddity.

Tim smothers the smirk that wants to bloom as he shrugs his jacket off, revealing the frilly white blouse beneath. It’s inappropriately sheer, but not enough that it can be called unprofessional, especially on a Casual Friday. Just enough opacity to be meaningful without fully concealing the bright red bralette he wears beneath. The pattern of the lace presses against the blouse, making its texture as obvious as the hue, which matches Damian’s face by now.

Stubbornly, he remains silent, searching his computer to check for the event he supposedly missed in lieu of a proper response.

Tim had only put the item in minutes prior, which Damian can undoubtedly see, but his lack of bluster when he reads aloud, “One-on-one session,” can only mean he’s catching on to the proceedings. Just in time for Tim to wind around the side of the desk and catch him with his pants down. Literally.

The tails of Damian’s untucked shirt barely cover his straining erection, and something in Tim positively soars at the idea that his presence hasn’t softened it in the least. He entertains the idea, briefly, that it might have even gotten harder.

“You—” Damian spits before he can fully form an accusation. In the hanging silence, Tim crosses his ankles and puts his hands on his hips, making it hard for Damian to pick any one spot to stare at that isn’t damning evidence and so forcing him to look Tim in the face. “You ought to have _knocked,_” he complains, sounding perfectly childish.

Tim lets the other’s exasperation and lack of confidence build on the pleasant sensations already roiling in his blood, like something high-octane and ready to burst. Damian, sitting in his chair with his thighs clenched tight as if to hide evidence he simply can’t, is most certainly the flame.

“That’s not very becoming behavior of a CEO,” Tim says, feeling his own pupils blow at the spill of color across Damian’s face darkening impossibly.

“Neither is dressing like a tramp,” Damian retorts. It’s still childish, and his immediate frown says he has acknowledged as such.

“It’s a good thing I’m not CEO anymore,” Tim says, sighing as he begins working at the buttons on his blouse. “Then I wouldn’t be able to do things like this.” _This _being the way he lets his shirt flutter to the floor, leaving him standing in the office with nothing on his upper half but a suggestive, cherry-red lingerie set. On the breast, a little Robin decal pinned with wicked intent.

The blush on Damian’s face suddenly drains, and Tim knows he has him by the twitch beneath his shirt that’s so painfully visible it makes his own cock stir in his panties. Which reminds him, he’s being slow; he goes for the jeans next, unbuttoning and watching Damian’s adorably wide eyes shoot to his face again before settling on the wall beside them.

“Might I remind you the door is still open,” he says, voice hopelessly cracked.

“I’m aware,” Tim returns. He pushes the jeans beneath his hipbones, enjoying the sudden pull of Damian’s attention back to him. This time he doesn’t bother looking away, and Tim feels the rush of accomplishment like he would in the field when he’d accurately peg a running criminal. “I suppose that’s a problem for you,” he goes on, “considering this inappropriate conduct.”

“Tim,” Damian says, voice a warning. Although he hasn’t called him Drake outside of work in years, the fact he lets the name spill in a professional setting drives Tim’s arousal higher and higher. “If my father finds out about this—”

“Let me guess. You’re in big, big trouble?” Tim bends over and sweeps his jeans off his ankles, taking both heels with them. If anyone were to pass by the doorway, they would get an eyeful, for sure. The threat does little to calm the want pulsing in him, but in fact makes it that much more evident.

Damian can’t seem to work out a response. While Tim stands before him, jutting obscenely against the fabric of his panties, he admires the deer-in-headlights look his supervisor wears for as long as he dares before stopping him from rising by planting one fishnet-clad foot squarely between his legs. With light pressure, he layers his foot over Damian’s cock, trapping it beneath his shirt.

The gasp he earns makes that burning sensation inside him boil over, and from there he can’t stop himself from lowering himself into Damian’s lap, knees planted on the chair on either side of him. “It would be a bad idea to miss that meeting,” he says matter-of-factly as he grips Damian’s face in both hands and tilts it to brush their lips together. Before kissing him properly, he whispers, “You know, since both of us missing at the same time would be really suspicious.”

Damian opens his mouth to say something, but closes it the second Tim leans in with purpose. “A good CEO never misses a meeting,” he continues, delighting in the once-again accumulating pinkness on Damian’s face. “If you’re not careful, you could wind up on the chopping block, Mister Wayne.”

All at once, a growl escapes from behind Damian’s gritted teeth. He surprises Tim by dragging him in for the intended kiss himself, one hand fisted in Tim’s hair to hold him still. There’s an adorable lack of experience there, but the ferocity with which he works more than makes up for it.

While Damian holds his hair, Tim hungrily trails his own hands down Damian’s chest, tugging insistently at buttons as he goes. With effort, he makes his way down the trail, popping the last button with a dismaying sound of threads tearing. Soon after, the clatter-and-roll of a plastic bit hitting the wooden floor. Against his mouth, Damian grunts. Tim can’t help but smile.

He rolls his hips against Damian’s, feeling the heat of his cock through the thin layer of fabric separating them now that the shirt is pushed out of the way. Despite himself, Tim moans at the size, wondering, not for the first time, when the kid had gotten so damn big. Right now, the only thing he can even focus on is the desire to get it in his mouth, feel the weight of it on his tongue.

With single-minded determination, he shimmies down Damian’s front until he’s crouched between those broad thighs, a hand on each one to keep him spread open. He hears the bitten-off sound from above him, making his mouth water, and wastes no time curling his hand around the base of the impressive length.

“You could have at least moved the mirror,” Damian all but whines as he white-knuckles the arms of his chair. “They can—” a pause, a gasp— “see you from the hall in the reflection.”

Tim’s resulting grin tells Damian everything he needs to know: That it had been a calculated decision not to move it, putting them both on display to anyone who happened to walk up the corridor. At the thought of being caught, lips stretched obscenely around his boss’s cock, his skin begins tingling again, pushing him toward the tip with a coquettish lick of his tongue.

Reacting automatically, Damian attempts to open his legs wider, unable to do so with his slacks in the way. The noise of frustration he makes warms Tim from the inside out, but the one after it, when he takes the head in his mouth and gives a particularly vicious suck, trumps every soft gasp before it. Damian moans so prettily, so unabashed at just the slightest touch that Tim has no other choice but to assume he’d never received oral before. Well, then, he thinks—he’ll take good care of him.

He goes down with intent, wetting each new inch with his tongue before sliding back to the tip each time, until the fifth descent has Damian jerking his hips toward the heat of Tim’s mouth, unable to stand the loss. He’s on top of the world once he begins stroking in time with his bobbing, and Damian moans again, stifling it with his knuckles pressed hard against his lips.

Tim takes the opportunity to look up at him through his lashes, wetness gathering on them from the reflexive tears as he removes his fist and sinks down to the base. Damian’s next sound is strangled, trapped in his throat as he puts tremendous effort toward not being heard.

After swallowing around him, Tim pops up and grins smugly when Damian’s hips stutter. Intently, he climbs back in the man’s lap and leans forward, showing off his ass to the mirror and anyone who happens to be lurking outside. He knows Damian can see the reflection over Tim’s shoulder. Knows how heated his stare is without even looking.

He starts by Damian’s earlobe, nipping his way along his neck and whispering against his skin, “You know, I’m ready to go if you are.”

Damian’s eyes flicker from the mirror to Tim’s face when he pulls back, and after a few seconds of mental catch-up, they go wide at the realization of what Tim means. Abruptly, strong hands tighten on his hips, holding him in place while Damian growls and ruts against him, brushing against the lace-clad underside of his cock until Tim shivers with the stimulation.

“One condition,” he says, feeling the laugh bubble up when Damian regards him suspiciously. “Don’t you dare schedule me any more paperwork.”

“You’re an idiot,” Damian breathes more than speaks. As much of an agreement as Tim’s going to get, he figures. Fine by him. He doesn’t need him to beg. Not today, anyway. He would like to see him try to act high-and-mighty now that Tim knows precisely how to unwind him from his ego.

He will admit he’s surprised when Damian takes initiative and hooks a finger underneath the scrap of fabric he’s wearing, pulling it aside enough that he can rut clumsily against Tim’s exposed hole. The glide is helped along by the lubricant he worked inside himself earlier with a well-timed bathroom break, and Damian seems to lose any remaining sense of hesitation the second he feels it.

Tim leans in again, hands on Damian’s shoulders to hold himself steady. The only visible indication of his own presence in the mirror is the curled ends of his hair; the rest is simply the arch of his back, pale skin and red lingerie, and the lewd display of his ass propped on the swollen tip of Damian’s cock.

The phone rings. Damian hisses a curse in his native tongue that raises goosebumps on Tim’s flesh. He waits, strategically parsing out the right moment to move.

On the line, he hears a tinny voice that could only be Bruce. “Son,” he says, berating in a way that makes Damian frown, “I’ve been informed you aren’t in your meeting.” Bruce doesn’t care. He has to pretend to care for the company’s sake.

The victory of Damian’s meager amount of shame at slipping a stupid meeting doesn’t compare to his face when Tim slides down on his cock, taking him in one go and sighing out his own pleasures just loud enough that he’s sure he can be heard over the line, given how close the phone is to his face.

Damian hooks his hand around Tim’s mouth in a talon-like grasp and spits into the receiver, “I have more important work to do than sit around listening to executives blather.” His eyes are narrowed, and there’s an obvious prayer in them that Bruce either hasn’t heard Tim or has somehow mistaken the nature of the sound.

The more pressing problem is that there are now footsteps in the hall.

Tim has never felt higher, soaring on the wings of Damian’s panic. It’s a rarity to see him so undone, and it’s almost better than the way he feels inside Tim, carving him open with a stretch so delicious he moans a bit louder than he means to against Damian’s palm.

“I trust you have your priorities in order,” Bruce says at length.

“I always do,” Damian replies, sounding strained.

Tim doesn’t hear their goodbyes, but he has heard enough to know Bruce doesn’t believe him at all.

The steps outside have stopped. He hasn’t yet heard them retreat. Meaningfully, he rises to the tip of Damian’s cock, his toes curling in his flimsy fishnets as he rocks his hips again, taking all of him with an exaggerated cry of enjoyment. Whispers in the hall now. Two voices.

He can’t keep the grin off his face, even though Damian is glaring daggers at him. His hand is still clamped tightly over Tim’s mouth and nose, to the point where he’s beginning to get lightheaded, but it doesn’t stop him from fucking himself down on him in earnest until Damian can’t help the groan that spills out.

“Someone is going to hear,” he mutters, as softly as he can.

Tim sees his eyes dart up to the mirror, knows how they appear in the shiny glass, completely visible to anyone willing to look. The second Damian removes his hand, Tim pants out an obscene, “Yes, Mister Wayne.”

The voices have caught Damian’s attention now, going by the upward tic of his brows. Even as gifted as he is, he’s having trouble figuring out a proper course of action with Tim riding him as hard as he is, muscles burning in his thighs. He doesn’t plan on stopping, not with the ghostly satisfaction of eyes on him as he takes his superior’s cock like it was nothing. He usually isn’t a fan of being the center of attention, but with his back to the door and only Damian’s debauched face visible in the mirror, he can’t say he isn’t enjoying giving a show.

But, then, his unfair advantage is stolen when Damian snarls and grips his waist, slamming him bodily down on his cock until he’s wailing. “You can do better than that, Drake.”

Tim makes a scandalized sound he’s ashamed to call a whimper. His calculated risk that Damian would be too embarrassed to admit it’d been Tim to take him apart has apparently fallen through, and now he’s as flayed-open and vulnerable as he had made his boss. Touché, he thinks, because that’s the only thing he can coherently piece together when Damian’s hips start pistoning into him, striking him in just the right spot over and over until he’s downright sobbing his yeses.

His face burns when the whispers become slick noises, and he realizes with a start that whoever is out there is getting off on them, too. It feels shameful now to be so exposed, especially when hands spread his cheeks and give their voyeurs more of a show.

“You’re such a prick,” he huffs, clinging to Damian’s expensive suit jacket for dear life.

And then, in his ear, quiet enough that the onlookers can’t hear: “I won’t be the only one reprimanded for this.”

_Oh._ Well, as far as Tim is concerned, it’s still a successful mission, even if they’re both humiliated. It is, at the very least, a tie.

The truly embarrassing part is the keening noise he makes when Damian pulses unexpectedly inside of him, maintaining his thrusts after the fact until Tim cums, hard, in the meager fabric of his panties where his cock is still trapped. The mess drips down the front of the lace long after his shudders subside.

When Damian lifts him off his dick with a vulgar pop, the voices outside groan faintly in tandem. Despite himself, Tim cranes his neck to peek in the mirror, getting a glimpse of what their company was seeing: His own flushed face, looking entirely fucked out. Worse, his pulled-aside panties revealing the mess that has been made of his hole, now raw and leaking cum. He instinctively knows that the pitched gasps from the corridor are their office voyeurs getting off on the fact of his ruin.

He moans softly against the lapels of Damian’s jacket, hiding his face once more. They’re both complete messes, which, after a moment of consideration, gives Tim another devilish idea. Ignoring his audience, he rolls his hips under the pretense of chasing the aftershocks of orgasm, wiping his own mess all over the front of Damian’s shirt.

“Actually,” he says, pretending to glance at the computer beside them, “I think you still have time to make that meeting, after all. I’ll go ahead and call Bruce to let him know.”

Damian pales immediately. “If you do, rest assured you’re on desk duty for the rest of your _life._”

Tim hums. “I think we can reach some kind of understanding.”

Laughably obvious despite the quickness of it, Damian’s eyes dart to Tim’s ruined outfit and back up before a scowl splits his face. “Fine,” he snaps. From the tone alone, Tim can tell he has won this round.


End file.
